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Dating Over 40: 5 Things You May Be Doing Wrong

A woman dating over 40 laughing to herself and playing with her hair.

If you’re dating over 40, you come to the dating scene with a lot of experience from your past loves and relationships. Sometimes that experience can work in your favor—you know what you want and are better at identifying when things are and aren’t working. Other times, however, your experience can work against you. Here are 5 things many people dating over 40 may be doing wrong.

1. Talking too much about your ex/exes
Let’s face it, if you’re over 40 and single, chances are you’ve already been in several relationships, if not a marriage or two. One of the first questions that usually gets asked after you meet someone is, “So, why are you still single?”

So, of course, you start talking about your ex or exes and how they were horrible, or how they cheated on you, which conjures up any number of bad memories, and suddenly you realize that you’ve spent your first date looking back instead of forward. You chatted aimlessly about the people you’re no longer with instead of trying to get to know the person right in front of you.

It’s normal to be curious about someone’s past, and I’m sure you’ll come across a date who will want to know more about your history. My advice is to spend minimal time talking about past lovers on your first date and spend more time finding out about the person you’re with. Telling someone how badly you were treated in the past might make them think there’s something more to the story you’re telling. For example, if you tell your date that you constantly got into fights with your ex, they might feel that the same thing could happen between the two of you. Or if you were cheated on, it may enter your date’s mind that there’s a reason for the cheating, and suddenly they’ll wonder about your compatibility, your state of mind, and any number of things.

Your past is past. Focus on the present situation and your current date.

2. Making the wrong fashion statement
Ladies: Did we forget what the word “lady” means?! I recently went out with a few friends for a drink. While in the bathroom, I overheard this woman who had to be in her late 40s talking to her friends about how she looks better than most 20-year-olds. I admit she looked good, meaning she was physically fit and had a pretty face, but she was wearing a mini-mini skirt with a cut-off shirt, and her breasts were virtually hanging out. Listen, I get it. You want to look sexy and feel young, but don’t give away the farm! How about just a nice, short skirt and a little cleavage? Let’s leave something to the imagination. Trust me, the guy will be able to see if you have a nice figure or not. Also, when it comes to perfume, why is it the older some women get, the more they put on? Try just spritzing on a nice, clean, mellow scent so the guy doesn’t choke to death. You don’t need to smell like you just bathed in it.

Men: It shouldn’t be that difficult for you to get dressed, but I see bad examples every day. You throw on a shirt with a pair of pants and shoes and you think you’re ready to head out the door. But take a good look at the button-down shirt you’re wearing—is it clean and properly pressed? Why go out in a wrinkled shirt and express your lack of know-how with an iron and board? Also, leave the ripped jeans at home until a second or third date. And I know sneakers are a big deal to a lot of you, but again, wait for a couple of dates before you sport your designer Nikes. Gentlemen, wearing a baseball cap on your first date is a fashion and personal faux pas, unless, of course, you are at a baseball game. If you’re doing this to hide your thinning hair or baldness, why not let your date see the real you from the start? Don’t be embarrassed, be proud of who you are! As with women and their perfume, don’t use the whole bottle of cologne on a first date—in fact, don’t do it ever.

3. Drinking to excess
I know the first date can be a little nerve-wracking, no matter what age. Believe it or not, I hear more stories about people in their 40s drinking a little too much on the first date than any other age bracket. I think it may be due to tension and nervousness, and the fact that maybe you’re just sick and tired of dating. First off, we all have to keep DUIs and safety in mind. Second, you’re old enough to know what happens when you drink a little too much. You may say something, or worse, do something you’ll regret in the morning. All I am saying is, pace yourself and be smart. Save the shots for another time.

4. Too eager or too indifferent
I think one of two things happen to us mentally when we date in our 40s. We either start to feel desperate, or we start developing an, “I’m fine on my own!” attitude. The desperate people who are dating over 40 and want to be married may come on a little too strong, or be so overly willing to please that they scare off their potential mates. Then we have those who think, “If it happens, it happens,” and won’t put honest effort into the date. Their dates are made to feel like these people don’t honestly care for them, and the lack of emotions indicate, if incorrectly, that settling down isn’t in their future. Egos really play a part here, and if there’s too much of it, the date can turn south quickly.

So just try to be the person in the middle. Don’t play the excited puppy dog, but don’t be the disinterested lazy cat lounging on the couch either.

5. Jumping in the sack too soon
I hear from many older women and men, “I’m an adult and I know what I’m doing!” Of course you do. I understand that you’re tired of being alone, and that you can use a good night of ardent, passionate, loving sex. I’m not questioning the fact that you’re an adult—I’m questioning whether you absolutely need to jump in the sack right away.

Sex more often than not means seeing one another naked. That is a huge step for two people who have just met. Real intimacy requires comfort and trust in one another, and it’s really hard to get those things after a two-hour dinner, or drinks at a bar. Try to get to know each other a little better. I think if you have sex too soon, it can interfere with getting to know the real person. Lust has a way of making us forget everything else, and that includes personal feelings.

Try to keep the date PG-rated, okay? Yes, we are all adults, but that also means we should have a level of maturity that allows us to hold out for a while and not succumb to carnal desires just yet.

As we get older, we tend to overthink the dating process since we have a larger frame of reference than a 25-year-old. If we remember to relax and be ourselves while keeping in mind the advice above, I’m sure good things will follow.

To read more of Tonia’s work and learn about her upcoming memoir, visit or follower her on Twitter at @ToniaDeCosimo.

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